Woke Man in a Dress

Bob the Drag Queen handles crowd work with the ease of a veteran schoolteacher, commanding the stage out of drag and letting his dry wit do the heavy lifting. The title comes from a real online comment calling him a “woke man in a dress,” a label he wears with pride as he leans into the generational divide and the oddities of modern culture. Filmed at Comedy on State in Madison, Wisconsin, the 73-minute set was released in June 2023. At this stage in his career, the RuPaul’s Drag Race winner was already a highly sought-after multi-hyphenate, busy co-hosting the Sibling Rivalry podcast and preparing to serve as the master of ceremonies on Madonna’s Celebration Tour. The material touches on his mother’s childhood warnings and the differences between gay men and lesbians on vacation, alongside a segment where he explains dial-up AOL and swapping CDs in a moving car to a bewildered Gen Z audience member. The special won a Webby Award in 2024 for Comedy Video & Film, and the audio version was named Comedy Album of the Year by The Interrobang.